Mishaps Worth Remembering
by IrishSwan
Summary: Based on my own Prompt #50: Killian is in the middle of a prank war with his friends. Killian also has a massive crush on Emma Swan. The day he decides to finally tell her how he feels and ask her out on a date, his friends (coincidentally) slip a Viagra pill into his coffee before he leaves. He doesn't realize what's happening until its too late…


**This story is dedicated to the lovely _Captainwiley_! I hope this cheers you up, and makes you laugh.**

 **Thank you to the amazing _So Much Tea_ for reading it over and for helping me make it funnier!**

 **I hope you all like it!**

For the past three years or so, Killian and his friends have been locked in this weird, long-term prank war. No rules, no limits, no mercy.

Unfortunately, this ongoing war was between himself, his brother and roommate, Liam, and his other two friends Jefferson and Robin. His friends of the female variety were adamant on only being spectators, finding pleasure at their expense.

For the first year, he didn't see much of a down point to this; it wasn't like Ruby, Elsa, or even Regina were the type to fully embrace the concept of laughing at oneself. But then Emma joined the band of misfits.

Emma, oh Emma. What was there not to like? She was funny, smart, tough and bloody gorgeous, both inside and out. He'd been pining after her for years, almost always brave enough to ask her out, but never too brave as to actually go through with it. That was about to change, though.

Today was the day. He was going to do it. He was going to finally, _finally_ , ask out the woman of his dreams.

He pushed himself out of bed, and practically skipped his way into the bathroom, calling out for his brother to fix him a cup of coffee while he showered.

* * *

This was his chance. His brother was preoccupied in the shower, and this was the perfect opportunity to get him back for what he did to him last week.

His idiot younger brother put together a little montage of his drunken antics and showed it to all of his friends. Not to mention, his _girlfriend_ , and any random bar patron who happened to be watching as well, in celebration of his birthday. And if that wasn't bad enough, his cake was a miniature molded Liam, sleeping nude in a public fountain.

Bloody git.

So now it was his turn, and he knew exactly what he wanted to do. He texted his mates, Robin and Jefferson, to come over, so that they too could witness the comedic goldmine that was about to become his younger brother, Killian. He also needed them to pick up a little something for his revenge.

They arrived, thankfully, before his brother emerged, dressed and ready to start his day. His friends practically broke his door down in their excitement to watch this prank unfold. With exactly three minutes to spare, they crushed a single Viagra pill and swiftly mixed it into his coffee. They figured the added milk and sugar would mask the feeling or taste of the powdered aid.

* * *

Killian walked into the kitchen with a spring in his step. He was excited to tell his brother of his newfound courage. Upon his entry, however, he found his kitchen crowded with three male figures, huddled together and giggling like schoolgirls on the playground.

Whatever they were up too, it could wait. Today was about him and Emma, and _nothing_ would change that.

"Good morning, lads!" Killian shouted in one of their ears.

"Bloody hell, brother." Liam started to chastise, but the grin overtaking Killian's face threw him off. "What's got you all smiley?" he asked.

Killian took a sip of his coffee before answering. "Well, since you're all here, I might as well share-" He stopped to take several gulps of his coffee, all three men sniggered at the action. "I don't know what's got you lot acting like fools, but whatever it is, I don't care. I'm going to ask Emma out to dinner with me. Tonight."

Suddenly, all three men stopped laughing and stood shocked in front of him, mouths agape, and eyes wide.

"Kill-" Robin tried to stop him, tell him he should delay his plans, but Killian was having none of it.

With one last down of his drink, Killian placed the now empty cup in the sink, and shouted over his shoulder on his way out of the apartment. "No, I don't want to hear it, mate. Emma's expecting me over and it's bad form to keep a lady waiting."

With that, he grabbed his coat and left his home, leaving behind three shell-shocked, mortified men in his wake.

* * *

"Ruby!" Emma yelled, "Ruby, he'll be here any minute and the living room's a pigsty. Help me clean up, or shove it into some other ro- Ruby get your ass in here!"

Ruby rolled herself out of bed and trudged into their small living room. "What." She didn't even bother phrasing it as a question.

"Help. Me." Emma stressed.

"I don't get what all the fuss is about, it's just Killian." Ruby shrugged nonchalantly.

"Yeah, to you. You know how I feel about him, though. So stop being a bitch and help me clean up your mess before he-"

 _Knock knock knock._

" _Shit!_ " Emma whisper-screamed in Ruby's direction.

"Don't worry, I got this. You just go answer the door." Ruby instructed. She picked up everything in a heap and moved in the direction of her bedroom. "Oh, and Emma?"

"Yeah?"

"Try not to jump him on sight, okay?" Ruby laughed as Emma threw a pillow at her from her place by the couch.

Once she was sure Ruby was out of sight, she ran to the mirror, fluffed her hair and checked her reflection for anything out of place, before she opened the door.

"Hello, love," Killian greeted her.

"Hey, Killian! Come in." She gave him a hug as he crossed her path.

"Sorry I'm late, my Liam was being weird, then traffic seemed to be at odds with me today," he said as he made his way over to her couch, just like he'd done hundreds of times over the course of their friendship.

"Oooo..." she grimaced, "How long were you stuck for?"

"About twenty minutes? Granted, it's not much, but it's still double the time it usually takes me to get here," he responded.

"Offf, that's rough." She said as she followed him to the couch.

They were sat side by side on the couch, laughing and talking about random things (as always) for only a few minutes before he felt a bit funny.

"If you'll excuse me, love, I just need to visit the lavatory real quick."

"Oh, alright, do you want tea or something?" she asked.

He didn't have the heart to tell her he'd already had his share of coffee. So instead he smiled and said, "Tea would be lovely, thank you."

* * *

"Shit!" Liam exclaimed a few minutes after his brother had left, "Shit, shit, _shit_!"

"This isn't going to end well," Jefferson supplied.

"No shit, Sherlock." Robin smacked the back of Jeff's head.

"What do I do? _Shit_." Liam was full on panicking at this point.

Robin, being the levelheaded one of the group, offered, "Well, first, you're going get your shit together. Then, we are going to try and catch up to your brother and stop him from making an arse of himself in front of Emma."

"Yes… yea.. uhh, yup, let's go." Liam dashed out the door, his friends not too far behind him.

They made it to the car and onto the road in record time, only to get stuck in heavy traffic.

"Robin, we'll never get there in time!" Liam exclaimed.

"Mate, get a hold of yourself. If we're stuck, he could be stuck too. Just text him, tell him not to go in." Robin advised.

"You don't understand, mate. Killian.. I - I never thought he'd be able to move on from Milah and everything that happened with her. I can't be the one to ruin his second chance. How the hell am I supposed to calm down!" Liam rambled on and on to himself. At some point, Jefferson just gave up on Liam and texted Killian from his own phone.

 _ **Mate, if you read this**_ **don't** _**go to Emma's. Prank gone haywire, call me and I can explain.**_

* * *

Just as Killian closed the bathroom door, he felt his phone ding. It was a message from Jefferson, but he couldn't be bothered with it at the moment. He put his phone face-down on the counter and threw a bit of water on his face.

 _What the bloody hell was going on?_

It was the feeling, low in his gut. It kind of felt like arousal? He wasn't sure. He knew Emma was bloody gorgeous, probably the most beautiful woman he'd ever met, but even he had better control of himself than that. But sure enough, images of Emma started to float through his mind, and with every new image, his shaft twitched just a little bit.

Before he knew it, he was hard. Painfully hard.

 _What on earth..?_

This had never happened to him before. He wasn't a young lad; the thought of a girl alone wasn't enough to get him into this state. Suddenly, he got an aching suspicion all the chuckling this morning was linked to this somehow. He didn't know how, but he was sure his friends were involved.

He flipped his phone over and looked at the message. He called his friend right after.

"Hello," Jefferson greeted on the other end of the line.

"What the bloody buggering hell did you do?!" Killian dove straight to it.

"Uhh.. Well- I- he- _we_ maybe sort of-" Jefferson stalled, trying to think of the best way to explain the situation, but was cut off by Killian's roar of-

"Spit. It. Out. I'm in her bloody bathroom. Stop wasting my time."

Liam grabbed the phone from Jefferson and decided to take responsibility for the mess, "Brother, I'm sorry. This is all my fault. IputViagrainyourcoffeethismorning."

"What." Killian deadpanned.

"I said, I may have dosed your coffee with Viagra, but Killian I swear I had no idea you were seeing Emma today, I-" Killian cut the call before Liam's apology could carry through properly.

He was trying to think of what to do, when a knock sounded on the door,

"Killian, you alright in there? You've been in there for quite a while,.." He could hear the worry in her voice.

"Sorry, love. I'll be right out."

He took a deep breath before opening the door and hobbling his way back to the living room. Luckily, she was sitting with her back to him. It made it a whole lot easier to grab his coat to shield his erection from her.

"Oh, there you are! Everything alright?" Emma asked, taking note of the pained expression on his face.

"Peachy," was all she could muster in reply.

"Your tea got cold while you were away. Come, let's make you a new one," she suggested.

Just the thought of standing up made his groin recoil in protest.

"No, love. It's fine, really." he insisted.

"C'mon, it's really no trouble." She said, suddenly noticing the coat on his lap, "Oh, I'm so sorry! Let me put that away for you."

 _Shite,_ he thought. "It's really alright, Emma."

"What's gotten into you today?" She really was confused at his behaviour. Without much warning, she reached out and grabbed his coat. In her haste to move the coat away from him, she had her back turned before she could notice the bulge he was sporting.

He almost wet himself. It was a close call. Quickly, he reached for the first thing he could find; an… empty popcorn bowl? _Bloody hell._

Using the bowl as protective armour, he sideways walked to the kitchen with his back towards Emma, who happened to turn around in time to see his odd display.

"Uhhh... Killian? What in God's name are you doing?" she chuckled.

"I uhh- I started this new workout routine. I heard walking this way helps build leg muscles." He cringed as the words left his mouth.

"Okay, weirdo." She smacked his butt as she passed him, causing him to jolt in response.

He made it to the kitchen without her noticing his predicament. Unfortunately, his problems only worsened from there. He was now devoid of cover, once more.

He looked around for anything that could possibly aid him. But Emma turned towards him before he could think through any of his options. He ended up holding a cookbook to his crotch.

"I didn't know you were into cooking?!" Emma exclaimed.

"Ah, yes! I have been dabbling in the culinary arts as of late." At least this response made sense, he thought.

"Well, you're just full of surprises today aren't you?" She sounded impressed. _If she only knew._

He was granted a few minutes of peace while they waited for the water to boil. However, their brief kitchen ramblings were much shorter than he would've liked. Not just because of his tightening pants, but he also really was looking forward to spending time with Emma today.

Before he was ready, the water was boiled, and his tea was set. Emma gave him his mug and told him to meet her back in the living room in just a moment; she needed to put away the used popcorn bowl.

Her kitchen had two doors, one leading to the living room, and the other to the hall by the exit. He always confused the two. Being the ponce that he is, he not only took the wrong door, but he also left the damned book on the counter. So when he heard Emma's footsteps close behind him, he turned so he was facing the coat rack.

"Whatcha doing now, crazy pants?" She asked. Did she really need to use the phrase ' _crazy pants'_ right now? God.

"Admiring your coat rack, of course. It has such lovely… arms." _Stop talking, stop talking, stop talking._

"Okay.. then? Come join me in the living room when you're done admiring its _arms_." Emma just gave up at this point.

He sideways walked back into the living room with his back to her. "Gotta honor the workout, Swan."

He drank his tea from behind the couch, one arm on the cup, the other around Emma. "You're so comfy from this angle, love."

Then, he tottered his way back into the lavatory. "I'll be back in a moment."

Except, he wasn't back in a moment. Not even several moments. He just stayed in there for another thirty minutes, trying to think of a plausible excuse to leave without hurting her feelings. But in his efforts to spare her, he seemed to have hurt her anyway.

He limped out of the bathroom and headed straight for the couch, hoping to find a pillow to cover himself with while he explained to her what was really going on. He decided she deserved no less than the truth. But he ended up sitting on that couch alone for a while before he realized she wasn't joining him.

He waddled his way to her bedroom and knocked before entering.

"Welcome back to the land of the living." Her words were humorous but her tone spiteful.

"Love, I'm sorry, I didn't mean to leave you waiting. I just..." He knew he needed to tell her, but he was afraid of her reaction. He decided maybe showing her would do the trick, so he just dropped the pillow.

"What! Oh my God, Killian, wha..I- you- huh- wha.." she was speechless.

"You see, lady Swan, I have to make new friends." He moved closer to where she was sitting on the bed.

"What do your friends have to do with this?" She was really confused, but didn't move an inch.

"Well, you see, I've probably ruined my chances now, but I came here to ask you to dinner. A date.. with me." He could feel her about to interrupt but quickly continued. "You see, my brother is a daft fool, thought it would be hilarious to add some Viagra to my breakfast. He didn't know of my intentions, and it does take awhile to take effect, so I didn't realize what was going on until I made it here. Being the gentleman that I am, I did not wish for you to be subjected to my... well-" He gestured to his tented pants. "Not until we've officially gone on a date at least."

"Wait, wait... So you expect me to believe your brother drugged you and didn't tell you and that's why you spent like a million hours in the bathroom instead of with me, and that it is the reason you're sitting in my bedroom with a boner, but you don't want to do anything about it because we haven't been on a date?" Emma questioned him and his sanity.

"Yes?"

With that Emma burst out laughing, and laughing and laughing. He didn't think she would ever stop, and if he was honest, he didn't really want her too. She hadn't kicked him out, or fled herself, so he took that as a win.

In the midst of her fit, he pulled her across his lap so that her back was cradled against his arm and her legs swung off the other side of his lap. Her laughter subsided into bouts of giggles when he spoke-

"Swan," he whispered into her hair. "Please tell me you still want me in your life."

She snuggled into his chest, to his discomfort and his pleasure, wiggled purposefully against his rigid member.

"Bloody minx."

Then said, "Killian, ask me out."

"Huh?" He had heard her perfectly clear, but he couldn't believe it.

"Ask me out." She repeated.

This time, he obliged, "Emma _Minx_ Swan, will you do me the greatest honor and go on a date with me this weekend?"

Instead of verbally responding to his request, she leaned forward and brushed her lips against his. He couldn't believe she was actually kissing him, but that didn't stop him from kissing her back. It started as a soft brush of the lips, but soon turned into a full on makeout session, with him lying on top of her on her bed, slowly grinding into each other.

The first time she felt his hardness make contact with her, she couldn't stop herself from losing her mind laughing again.

"Love, it's bad form laughing at a man in this state,"

"I'm sorry, I'm sorry. It's just- Viagra?" She laughed again, "After two years, all it took was your brother putting Viagra in your coffee to get you in my bedroom? To get you to finally ask me out?" This time he joined her when she laughed.

He was so bloody happy, he just nuzzled his face in the crook of her neck and started kissing every patch of skin he came into contact with, until he got her full attention back.

It was a crazy situation but about a year later, Liam would share this story with all their friends and family, as the best man at his and Emma's wedding.


End file.
